US4424348A
Expired / Lapsed
US
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Methods of manufacture of nitrile-containing glucuronic acid conjugates
Assignee: CENTURY SCIENCE CORP 99 SOUNDVIEW DRIVE PORT WASHINGTON NEW YORK 11050 A CORP
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Filing: 1978-10-13
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Granted: 1984-01-03
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Expires: 1998-10-13
Abstract
Abstract Mandelonitrile- beta -D-glucuronic acid is produced by condensing a mandelic amide with a tri-O-acetyl methyl ester of glucuronic acid and then reacting the product with acetic anhydride to produce the tri-O-acetyl methyl ester of mandelonitrile- beta -D-glucuronic acid. The protecting acetyl groups may be removed and the barium salt formed by reacting with barium hydroxide, which salt, when treated with sulfuric acid, will yield the mandelonitrile- beta -D-glucuronic acid. This compound, as well as methacrylonitrile beta -D-glucuronic acid may be used in the treatment of bacterial infections having beta -glucuronidase activity.
Inventors
- 👤 David Rubin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:19
CPC Classifications
A; A61; A61K; A61K51/00; A61K51/02; A61K51/04; A61K51/0491; A61K31/00; A61K31/70; A61K31/7004; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/549; C; C07; C07H; C07H15/00; C07H15/18; C07H15/20; C07H15/203; C12; C12Q; C12Q1/00; C12Q1/34; G; G01; G01N; G01N33/00; G01N33/48; A61K2123/00
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
106 words
A method for the production of mandelonitrile-β D-glucuronic acid, comprising: condensing mandelic amide with methyl (tri-O-acetyl-α-D-glucopyranosyl)halide-uronate to form the methyl ester of mandelic amide-tri-O-acetyl-β-D-glucuronic acid; reacting the product of said condensing step with acetic anhydride at a sufficient temperature and time to produce the methyl ester of mandelonitrile-tri-O-acetyl-β-D-glucuronic acid; adding to the product of said reacting step a sufficient quantity of barium hydroxide to produce a white precipitate; separating said precipitate; treating said precipitate with a sufficient quantity of sulfuric acid until precipitation of barium sulfate is completed; removing the supernatant from the product of said treating step; and drying said supernatant to obtain mandelonitrile-β-D-glucuronic acid.
Claim 2
Independent Claim
106 words
A method for the production of mandelonitrile-β D-glucuronic acid, comprising: condensing mandelic amide with methyl (tri-O-acetyl-α-D-glucopyranosyl)halide-uronate to form the methyl ester of mandelic amide-tri-O-acetyl-β-D-glucuronic acid; reacting the product of said condensing step with acetic anhydride at a sufficient temperature and time to produce the methyl ester of mandelonitrile-tri-O-acetyl-β-D-glucuronic acid; adding to the product of said reacting step a sufficient quantity of barium hydroxide to produce a white precipitate; separating said precipitate; treating said precipitate with a sufficient quantity of sulfuric acid until precipitation of barium sulfate is completed; removing the supernatant from the product of said treating step; and drying said supernatant to obtain mandelonitrile-β-D-glucuronic acid.
Claim 3
Dependent Claim
2 words
Methacrylonitrile-β-D-glucuronic acid.
Claim 4
Dependent Claim
2 words
Methacrylonitrile-β-D-glucuronic acid.
Claim 5
Dependent Claim
30 words
A method in accordance with claim 1 wherein said condensing step is accomplished in solution in quinoline, phenol, methyl nitrile or methyl cyanide catalyzed by silver oxide or siver carbonate.
Claim 6
Dependent Claim
25 words
A method in accordance with claim 1 wherein said condensing step is accomplished in aqueous acetone solution in the presence of sodium or potassium hydroxide.
References Cited (Backward Citations)
DE2212014A1
Cited
DD122386A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-01-02 | 1987-07-04 | 1988-01-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-02 | 1991-07-04 | 1992-01-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-02 | 1995-07-04 | 1996-01-03 | $7700.00 | Window Closed / Lapsed |